CAS: 550-33-4; (2R,3S,4R,5R)-2-(Hydroxymethyl)-5-(9H-Purin-9-yl)Tetrahydrofuran-3,4-Diol

该化合物是天然产生的核素,产自纯碱基腺,其特征为结构构成,其中包括与基相连的糖,其作用在各种生物过程中值得注意,并已研究其潜在的治疗用途,特别是在抗病毒和抗癌症研究领域;复合水体中溶解性,这有利于其生物活动;其分子结构允许与核酸相互作用,影响细胞机制;此外,对内核素进行了调查,以了解其对酶活动的影响及其调节免疫反应的潜力;虽然在临床环境中没有广泛使用,但目前正在进行的研究继续探索其药理特性和可能的医学应用;同许多核素制剂一样,其稳定性和再活性可能受到诸如pH和温度等环境因素的影响,使其成为生物化学学和药理学进一步研究的有趣课题.

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4546-54-7 58-63-9 21138-24-9

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CAS号15981-63-2 (3,4-diacetylox... | CAS号120-73-0 嘌呤 | CAS号58-96-8 尿苷 | CAS号79366-24-8 9-(2,3,5-tri-O-... | CAS号574-25-4 6-疏基嘌呤核苷 | CAS号7387-57-7 2',3',5'-三乙酰腺苷 | CAS号290-87-9 1,3,5-三嗪 | CAS号6001-15-6 N1-(β-D-ribofur... | CAS号5746-27-0 2-(6-hydrazinyl... | CAS号6974-32-9 1-乙酰氧基-2,3,5-三苯... | CAS号29618-02-8 6-hydroxymethyl... | CAS号29699-93-2 1H-Purine-6-met... | CAS号15981-63-2 (3,4-diacetylox... | CAS号13754-19-3 4,5-二氨基嘧啶 | CAS号120-73-0 嘌呤 | CAS号53303-84-7 CPUMP SODIUM SALT | CAS号64-18-6 甲酸

合成工艺路线路线简述

    📜2',3',5'-三乙酰腺苷置于亚硝酸特丁酯,氨体系中,用 四氢呋喃,甲醇 作为反应溶剂,化学反应 0.33H,反应生成 9-(β-D-呋喃核糖)嘌呤
    参考文献:核酸相关化合物.116.氨基嘌呤核苷的非水重氮化.机械方面的考虑和使用亚硝酸叔丁酯或亚硝酸钠的有效方法.
    标题:核酸相关化合物.116.氨基嘌呤核苷的非水重氮化.机械方面的考虑和使用亚硝酸叔丁酯或亚硝酸钠的有效方法.
    摘要:研发了两种类型的氨基嘌呤核苷衍生物的非水重氮化-重氮化.检查了用sbcl(3)/ Ch(2)cl(2)处理9-(2,3,5-三-O-乙酰基-β-D-核呋喃糖基)-2-氨基-6-氯嘌呤(1)氯化苄基三乙基铵(btea)作为可溶性卤化物源,亚硝酸叔丁酯(tbn)或亚硝酸钠作为重氮化试剂.用sbcl(3)获得2,6-二氯嘌呤衍生物的最佳收率(> 80%).与sbbr(3)/ Ch(2)br(2)组合得到2-溴-6-氯嘌呤产物(> 60%),Sbi(3)/ Ch(2)i(2)/ Thf得到2-碘-6-氯嘌呤衍生物(> 45%).三卤化锑催化非常有益.混合组合(sbx(3)/ Ch(2)x'(2); X / X'= Br / Cl)得到2-(溴,氯,和氢)-6-氯嘌呤衍生物,它们取决于反应条件.碘乙酸(iaa)的加入导致嘌呤自由基种类转移为2-碘-6-氯嘌呤衍生物,同时其他自由基衍生产物也相应
    DOI:10.1021/jo0204101

    海关参考信息

    专利信息


    专利号:US-9884885-B2
    优先权日:2009-05-18
    标题:Synthesis of labile base protected-modified deoxy and modified ribo nucleosides, corresponding phosphoramidites and supports and their use in high purity oligonucleotide synthesis
    发明人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
    权利人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P; CHEMGENES CORP
    摘要:This invention relates to novel method of synthesis of RNA utilizing N-2-acetyl protected guanine as nucleoside base, nucleosides, succinates, phosphoramidites, corresponding solid supports that are suitable for oligo deoxy nucleosides and RNA oligonucleotide synthesis. Our discovery using N-acetyl protected guanine as nucleoside base protecting group, which is significantly faster base labile protecting group, yet significantly more stable than commonly utilized-2-isobutyryl guanosine is a novel approach to obtain highest purity oligonucleotides. This approach is designed to lead to very high purity and very clean oligonucleotide, after efficient removal of the protecting groups, including acetyl group from guanine and to produce high purity therapeutic grade DNA oligonucleotides, RNA oligonucleotides, diagnostic DNA, diagnostic RNA for microarray platform. The deprotection of acetyl protecting groups of the natural deoxy and ribonucleosides occurs under substantially reduced time in contact with mild deprotection conditions such as mild bases, secondary amines for removal of such groups under such conditions would allows synthesis of various DNA and RNA of highest purity for diagnostics and therapeutic application. This approach is designed to lead to high purity large scale therapeutic grade oligonucleotide chimeras which consist of fluoro sugar modification in conjunction with deoxy nucleosides, ribonucleosides, modified base and modified sugar nucleosides. This approach is further designed to use acetyl guanine protecting group when other bases are sensitive nucleoside, and for use in oligo peptide synthesis and for support bound oligo nucleotides.

    专利号:US-8981076-B2
    优先权日:2008-11-29
    标 题 :Synthesis of N-FMOC protected deoxy nucleosides, ribo nucleosides, modified deoxy and ribo nucleosides, and phosphoramidites, and their use in oligonucleotide synthesis
    发明人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
    权利人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P; CHEMGENES CORP
    摘要:This invention relates to synthesis of novel -N-FMOC protected nucleosides, succinates, phosphoramidites, corresponding solid supports that are suitable for oligo deoxy nucleosides and RNA oligonucleotide synthesis. Our discovery using N-FMOC as nucleoside base protecting group, which is highly base labile protecting group is a novel approach to obtain highest purity oligonucleotides. This approach is designed to lead to very high purity and very clean oligonucleotide, after efficient removal of the protecting groups and to produce high purity therapeutic grade DNA oligonucleotides, RNA oligonucleotides, diagnostic DNA, diagnostic RNA for microarray platform. The deprotection of FMOC protecting groups of the natural deoxy and ribonucleosides occurs under very mild deprotection conditions such as mild bases, secondary and tertiary amines for removal of such groups under such conditions would allows synthesis of various DNA and RNA of highest purity for diagnostics and therapeutic application. This approach is further designed to use FMOC protecting group on various base sensitive nucleoside, and for use in oligo peptide synthesis and for support bound oligo nucleotides. DNA oligonucleotides containing 3′-end dA at the 3′-terminal will be produced using the FMOC-dA-supports would lead to much reduced M−1 deletion sequences, and thereby high purity.

    专利号:US-6048975-A
    优先权日:1991-09-12
    标 题:Process for the chemical synthesis of oligonucleotides
    发明人:PFLEIDERER WOLFGANG; BERGMANN FRANK
    权利人:HOECHST AG
    摘要:A process for the chemical synthesis of oligonucleotides n Use of a dansylethoxycarbonyl group as base-labile 5'-hydroxyl protective group in the chemical synthesis of DNA and RNA and suitable synthetic processes. n The ease of detection of the dansyl protective group and the ease of elimination from the sugar residue of the nucleotide without side reactions make oligonucleotide synthesis possible with high yields in very small quantities.

    专利号:US-10167308-B2
    优先权日:2013-09-14
    标题:Highly efficient synthesis of long RNA using reverse direction approach
    发明人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
    权利人:CHEMGENES CORP
    摘要:The present invention relates to novel process of reverse 5′→3′ directed synthesis of RNA oligomers in the range of about 100-mer to about 200-mer has been developed and disclosed. Using that method demonstrated high quality RNA synthesis with coupling efficiency approaching 99%.

    专利号:EP-1108724-B1
    优先权日:1996-01-16
    标题 :Synthesis of methoxy nucleosides and enzymatic nucleic acid molecules
    发明人:WINCOTT FRANCINE; BEIGELMANN LEONID; MATULIC-ADAMIC JASENKA; USMAN NASSIM; HAEBERLI PETER; KARPEISKY ALEXANDER; SWEEDLER DAVID; JARVIS THALE; DIRENZO ANTHONY
    权利人:SIRNA THERAPEUTICS INC
    摘要:This invention relates to chemical synthesis of 2'-O-methyl, 3'-O-methyl and 5'-O-methyl nucleosides, incorporation of novel chemical modifications in enzymatic nucleic acid molecules and improved methods for the synthesis of enzymatic nucleic acid molecules.

    专利号:US-2005130201-A1
    优先权日:2003-10-14
    标 题 :Splint-assisted enzymatic synthesis of polyribounucleotides
    发明人:DERAS MICHAEL; PLEISS JEFFREY A; SCARINGE STEPHEN
    权利人:DHARMACON INC
    摘要:The present invention comprises methods and compositions for splint-assisted enzymatic synthesis of polyribonucleotides using an RNA polymerizing enzyme. The invention provides ligating ribonucleotides comprising ligating a donor RNA molecule to an acceptor RNA molecule in the presence of RNA ligase and a splint, wherein the donor RNA molecule is comprised of at least one nucleotide and a ligation linker moiety, the acceptor RNA molecule is comprised of at least one nucleotide and a ligation linker moiety and the splint is comprised of a polyribonucleotide. The invention also provides splints for use in splint-assisted enzymatic synthesis using an RNA polymerizing enzyme.

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    主要参考文献


    1: Lougiakis N, Marakos P, Pouli N, Fragopoulou E, Tenta R. Synthesis of new nebularine analogues and their inhibitory activity against adenosine deaminase. Chem Pharm Bull (Tokyo). 2015;63(2):134-42. doi: 10.1248/cpb.c14-00731. 39(9):3607-11. 41(2):560-5. 40(5):771-84. doi: 10.1021/jm960605z. 204(2):1019-24. 377(2):263-8. doi: 10.1016/s0027-5107(97)00084-5. 14(16):6579-90. doi: 10.1093/nar/14.16.6579.
    8: Lüdemann HD, Westhof E. Conformations of the nucleoside analogs formycin, 2-azaadenosine, and nebularine in solution. Z Naturforsch C Biosci. 1977 Jul- Aug;32(7-8):528-38. doi: 10.1515/znc-1977-7-809. 33(5):1796-9. doi: 10.1021/jo01269a020. 23(14):2023-35. doi: 10.1016/0006-2952(74)90261-5. (12):1-4.
    6:643-8. doi: 10.1016/s0040-4039(01)99678-9. 7(2):94-8. Chinese. 61 Suppl

    合成参考文献


    摘要:DiRocco, D. A.; Schultz, D. M., Science of Synthesis: Photocatalysis in Organic Synthesis, (2018) 1, 615.
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